Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides

The concise synthesis of rhododendrol glycosides 3-8, which are novel derivatives of (+)-epirhododendrin (1) and (-)-rhododendrin (2), has been achieved in six steps from benzaldehyde 9. The key reactions include aldol condensation and trichloroacetimidate glycosylation. From biological studies, it...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-01, Vol.24 (1), p.122-125
Main Authors: Iwadate, Takehiro, Kashiwakura, Yutaka, Masuoka, Noriyoshi, Yamada, Yoichi, Nihei, Ken-Ichi
Format: Article
Language:English
Subjects:
Benzaldehyde
Butanols - chemical synthesis
Butanols - chemistry
Butanols - pharmacology
Dose-Response Relationship, Drug
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosides - pharmacology
Molecular Structure
Monophenol Monooxygenase - antagonists & inhibitors
Monophenol Monooxygenase - metabolism
Structure-Activity Relationship
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Summary:The concise synthesis of rhododendrol glycosides 3-8, which are novel derivatives of (+)-epirhododendrin (1) and (-)-rhododendrin (2), has been achieved in six steps from benzaldehyde 9. The key reactions include aldol condensation and trichloroacetimidate glycosylation. From biological studies, it has been determined that synthetic derivatives of 1 and 2 possess potent tyrosinase inhibitory activity. Particularly, the inhibitory activity of cellobioside 8 (IC50=1.51μM) is six times higher than that of kojic acid. The R-epimers (4, 6, and 8) possessed more potent activity than the corresponding S-epimers (3, 5, and 7), indicating that tyrosinase inhibitory activity is significantly governed by stereochemistry of rhododendrol glycosides.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.11.063